In Conversation: Jacquette M. Timmons

Jacquette M. Timmons is a Wall Street based financial behaviourist who works with everyone from the middle class to the 1%—helping them ‘blend the emotions of money with the math of money’. Jacquette is also the founder of Sterling Investment Management, Inc. and the author of Financial Intimacy: How to Create a Healthy Relationship with Your Money and Your Mate. Here, she talks to Libby about the ways we talk about money (or not), about the writing of the book, and about one of the most influential factors in her life. (Hint: it’s a person.)

Jacquette M. Timmons, image by Frederick V. Nielsen, II

Jacquette M. Timmons, image by Frederick V. Nielsen, II

Welcome, Jacquette. Can you start, please, by explaining what a financial behaviourist is, and how one would differ from, say, a financial analyst?

Many thanks for having me!

Behavioral finance is a field of study that seeks to combine psychology-based theories with finance to explain why people make the decisions that they do with their money. A financial behaviorist studies people’s behavior with money, and in my case, I blend the emotions of money with the math of money to help my clients achieve their life and financial goals—to, in essence, create a new financial reality.

A financial analyst is a researcher—someone who studies the macroeconomic, microeconomic and company-specific conditions in order to make investment recommendations. Their scope of work certainly impacts the field of personal finance, but they do not work directly with individual clients.

In your work and your writing, you pay a lot of attention to stories—such as the ones we have grown up with that stay with us into adulthood—but you also pay attention to the absence of stories and discussion, especially around our personal finances. What do you think we gain by talking about our financial situations with others, and which aspects do you think are important to discuss with others?

There are some that say talking about money is still a taboo topic. I push back on that; I say people talk about money all the time. They just aren’t having the right conversations about it. Typically, when people talk about money, the scope of the conversation is often confined to just the numbers, a particular transaction, or celebrating a win. People rarely boast about the stock or deal they lost money on. Rarer still is the conversation that goes beyond the numbers to explore values, beliefs, habits, expectations, fears, desires, and financial philosophy, discipline and character. In part, this is because a lot of people aren’t skillful when it comes to painting the picture of what’s happening in their financial lives while only divulging the details they feel comfortable sharing. So, instead of exercising this muscle, they opt for saying nothing. And when you say nothing, everyone loses. Because one of the best ways we learn about ourselves (and from others) is by sharing experiences.

… people talk about money all the time. They just aren’t having the right conversations …

That said, I also understand it: So much of our identity, sense of self-value and self-worth is tied up with money—how much we have as well as how much we don’t have, yet want. And even though everyone, regardless of where they fall on the income and wealth spectrum, has the same concerns when it comes to money, it never really feels that way. Because money feels both personal and private, you can feel like you’re the only one with your particular questions, challenges, frustrations, goals and aspirations. And if we were more open to talking about our situations and experiences with money—the successes and failures—we (a) wouldn’t feel alone, and (b) might just discover an alternative solution we hadn’t considered previously.

One of my ‘tools’ for reminding myself that I’m not alone and for getting a different perspective (because the path of entrepreneurship is perhaps my biggest money ‘teacher’) is by having an accountability group. It’s a space where I feel safe and secure to share what’s going on, and it helps me address my issues with money so that I can show up fully and be more present for my clients.

This is probably a good time to reference the mythologist, Joseph Campbell. He said, “Everything begins with a story.” At the end of the day, we all have a ‘money story’. If we could embrace the tangled emotions we have toward money as part of the story, and not the entire story of who we are as a person, we’d be better off individually and collectively. The perfect mirror for this is an accountability partner or group.

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Jacquette M. Timmons in action, screenshots courtesy of

Why did you decide to write your book Financial Intimacy for women particularly?

Financial Intimacy as both a notion and as a book evolved over time for me. It started with a pattern of choices I found perplexing.

The short answer to your question is this: While I wholeheartedly believe men need to be as financially self-aware as women and that financial intimacy starts first with you, I wrote it ‘for’ women because when the intersection of love and money goes awry we (women) tend to suffer the negative consequences thereof to a far greater degree.

But here’s the full story of why I focused my book on the experiences of women, in particular: I’m a single child. My dear friend, Deno, who was like the older brother I didn’t have and who was married to my college roommate, died in 2003, two days after his 41st birthday, of a brain aneurysm. As a result of his death, I saw up close how one’s grief can be interrupted by what you don’t know about your spouse (or significant other’s) personal finances.

In March of the same year, the father of another friend died. That’s when her mother discovered the family was $500,000 in debt—and that was not the mortgage!

In late April/early May, I was working with a coaching client who on paper was the epitome of financial success. Wharton MBA; worked on Wall Street earning a sizable six-figure salary; was smart about how she managed her money; yet fought all the time with her live-in-boyfriend over money. From our work, what we soon discovered was the reason had little to do with him and more to do with her not wanting to end up like her parents (or her brother and sister-in-law) when it came money.

Had these three events occurred with a little more distance between them, I may not have noticed anything. But given the timing, I began to wonder: “What are these smart, highly-educated, professional women, who manage other aspects of their lives well, not discussing during pillow-talk time that they have no clue what’s going on in their households when it comes to money?!”

Yes, their individual circumstances were quite different. But, fundamentally, they all made the same mistake. Once I noticed this in them, I began to expand my scope of vision and realized, wow, a lot of us (myself included) are making the same love and money mistake.

I found this fascinating, and I was curious—I wanted to know more about the ‘why’ and I wanted to see how I could help resolve it.

The book came after I first created a workshop—”Women, Money and Romance.” I realized that no matter how much I tweaked the content, format, length of time, it never seemed enough to address the questions that were being raised. It also became clear that women wanted a platform not just to vent, but also to be heard.

The book also came after I researched other books that were already out there about love and money. I realized there was a gap I could address: there wasn’t a book that (a) took a social critic’s look at the intersection of love and money and examined how/why it changed over the last forty years due to social, economic, cultural and familial shifts—as well as shifts in the personal finance industry; (b) focused on women of all different marital statuses; and (c) in my opinion, honored that there’s more than one way to live a life.

I wanted to write a book that explored the sweet spot of where the relationship you have with yourself, your money and your mate converged.

I wanted to write a book that would enable a woman to see herself—at some point in her life – in some of the stories of the women I profiled. And, hopefully, give her ideas of takeaways she could apply to her life to make navigating this vulnerable terrain a bit easier.

I also wrote it because I am hopeful. I am hopeful that money doesn’t have to be why so many couples break up. I want money to become the unlikeliest of communication tools that enables us to connect with each other more deeply—that allows us to learn more about each other and grow together.

When reading your book, I appreciated being able to see snapshots of other women’s financial pictures with their partner or spouse, but what also came through in the telling of these stories was your deep care and respect for the fact that all manner of relationships on the love and racial and gender identity spectrums exist. And, furthermore, that with a bit of investigation and work, a proactive financial plan can be found for any set of parameters or context. Where do you think this loving and respectful pragmatism, or ‘spirit’, comes from in your own life? 

Oh, without question, it comes from my mother.

Growing up, I didn’t appreciate what was different about our family. We left New York City when I was seven years old for a small college town in the Western part of New York State. A town that wasn’t very diverse; I was one of two black students in my entire grade school! My mother was separated, at a time when separation and divorce were not as prevalent (or socially accepted) as they are now. My mother was a professional musician and had toured and traveled across the country on the coffee-house circuit; even when she ‘retired’ from singing and started working for the Social Security Administration, she still sang locally. She was an anomaly of a working, single mother who didn’t entirely give up her life as an artist, but also made choices to ensure our financial security and stability. She also held the title of being the only female umpire in all of Western NY for many years (I inherited my love of the Yankees from her). And, although private about her sexuality, she was a gay woman. There weren’t many other students in my school or children in my neighborhood with a mother the likes of mine.

I think all that shaped my mother, her choices and how she approached the world—being accepting of people without judgment; being kind to everyone regardless of their station in life; always looking for the best in people (but not taking sh*t from folks, either)—I think that grace and tenderness trickled down to me.

So thank you, by the way, for noticing. I was well aware of the privilege I had in terms of bearing witness to the stories of the women I profiled—some of whom shared things with me they hadn’t with those closest to them. I was also keenly aware of the responsibility that came with that and it was my intent to honor that as best I could.

This idea of looking behind our own behaviours to understand what drives us is likely to be a familiar concept for those readers of The Woolf who are fiction or screen writers (and there are quite a few out there!), because it’s vital for any writer to learn the skills to dive deep—to understand how a character’s ‘backstory’, their cultural and geographic ‘storyworlds’, fears and desires inform their actions. But this is a far easier process when we, as author, can play God, and the mirror isn’t being held up to ourselves! To quote ‘Kim’, one of the interviewees in your book: “knowing our baggage is one thing; being able to shake the residual effect of it is quite another.” What would be your recommendations for those who want to take the next step, once they have reached an awareness that their own history and stories—and emotions—are driving their relationship with money?

I’d recommend two things: First, don’t judge your newfound insight as ‘good’ or ‘bad’. You could reach this stage of awareness and discover you actually have a healthy relationship with money, which of course is fantastic. But not if it causes you to operate as if there’s never room for improvement. The hard part here is not to become complacent; because when you do you overlook financial leaks and discount financial opportunities that are staring right at you—but you can’t see!

On the flip side, if you discover your relationship with money isn’t ideal or as you’d want (or need) it to be in order to achieve your goals, don’t get dismayed by the work that needs to be done to close the gap between where you are now and crossing the threshold to the other side. Know what needs to be done, but approach it a little at a time. I’m known for saying you can’t swallow the elephant whole without choking. So, I recommend working in 90-day increments.

…while money is never just about money, the numbers do tell a story…

Second, remember that while money is never just about money, the numbers do tell a story—a story about your choices, priorities, preferences, beliefs, expectations, habits, values and more. However, you can’t see the fullness of that story if it’s in your head and not on paper. Imagine how your relationship with money might change if you thought of it as a character in the story of your life. As a fiction or screen writer, what role would you have money play?

This may sound hokey, but here’s a big problem many people bump up against: they interact with money passively. The way you switch that paradigm and cultivate a more active relationship with money is to document your story on paper! Write down your goals, write down how much you want to save (and why); write down who and what you want to invest in (beyond the usual suspects of investment securities and real estate); write down how you’d spend your money if you had more money than you do currently; write down what you’d earn if you could wave a magic wand; write down your ideas of how you envision closing the gap between what you have and what you want; note what you want money to do for you as well as what you’re willing to do for it.

It absolutely starts with increasing your financial self-awareness about you and your relationship with money. But that is really just a springboard.


Image by Frederick V. Nielsen II, courtesy of

Why do you think it’s so important to continually revisit—and moreover discuss—our financial strategies, rather than opt for a ‘set and forget’ model, which could arguably work as a basic savings method? 

Because nothing about any of our lives is static. Something changes everyday—at times in subtle ways; at other times, quite drastically. Yet, we often fail to apply this awareness to how we approach money—even though it impacts almost every area of our lives.

I agree the ‘set and forget’ model can help with the discipline of saving and protect you from yourself in terms of not relying on the power of will. But that doesn’t mean you shouldn’t periodically re-confirm the account to which those funds are being deposited remains the best place for them.

The ‘set and forget’ model is particularly dangerous when it comes to electronic statements and investment accounts. With the former, you get the email notification, but never take ten minutes to review your statement. So you don’t notice double charges (I’ve been guilty of this) or subscription charges for services you no longer use.

When it comes to investing, the market naturally goes up and down. This fluctuation has an impact on your investment portfolio. So, let’s say you’ve determined you should have 75% stocks, 15% bonds, 10% cash. The market does what it does and now your allocation is 80% stocks, 10% bonds, 10% cash. Now, you have more exposure to stocks and less to bonds than you want. You won’t notice this if you aren’t paying attention and will, therefore, end up in a situation where you are over-exposed and under-exposed in ways that aren’t in alignment with your goals.

In my opinion, it’s all about engagement and being proactive. So, even if you determine no action is required, it’s better to have a review process in place. It helps to remind you why you’re doing what you’re doing the way you’re doing it!

Your book came out just after the 2008 financial crisis and the subsequent ‘credit crunch’. In the meantime, have you seen any core differences in people’s relationships with money, given the emergence of new technologies? And here I’m talking about the ‘instant’ mobile life, with online banking and online shopping apps, as a start, as well as the evolution of BitCoin and other alternative currencies

Yes, but the differences actually have less to do with technology than simply adopting a new perspective.

Interestingly, the 2008 financial crisis made it easier to spread my message about money not just being about money. When everything is going up and cash is flowing and you can’t seem to make a wrong financial move, it’s easy to discount the non-financial elements of money.

However, the crisis made everyone perk up and begin to pay attention to the behavioral aspects of money—their own, as well as those of other people, companies, and the government. Much more today than pre-September 2008, people are embracing the role of the psychology and emotions of money. They view doing so less as some woo-woo, new-age stuff, and more as a smart and strategic way to manage their money. Now, it’s cool and hip!

With regards to the emerging technologies, here’s an irony: The majority of the personal finance apps we each have access to today came on the market after the financial crisis. In fact, since 2008, US$9 billion dollars have been spent on what’s referred to as fintech—financial technology—for personal use. The challenge is to not confuse quick and easy access to your financial information with actually having insight that will help you make better decisions and choices about your money.

You wrote on your blog that ‘creativity thrives with parameters’. And yet many people would not think of financial planning as an especially creative pastime because—as you yourself have put it—’two plus two will always equal four’. At what point in your career did you start to value the link between creative thinking and financial planning? 

I probably first made the connection when I worked at Bankers Trust (now Deutsche Bank) in the private bank and I had to convince the hiring manager that there was little difference between designing a pair of shoes and creating a financial product.

In case you didn’t know, I attended the Fashion Institute of Technology. It was my goal to be a shoe designer. Before the first semester ended, I knew that wasn’t going to exactly pan out. So I switched my major to marketing. Six years later, armed now also with an MBA in finance from Fordham’s Graduate School of Business, I’m talking about the parallels between getting a pair of shoes into someone’s hands as being the same as getting a derivative into their portfolio. And it all made perfect sense to me.

Here’s why: Creative thinking and financial planning are both tools for achieving a result.

They both require you to pay attention to patterns; they both require you to connect dots (that may or may not be noticeable to others); they both require an imagination in order to see something other than the reality in front of you at the moment; they both require discipline; they both require you to produce an end result; they are both reiterative—creative thinking and financial planning are skills you must practice.

I’d also like to ask you about the book-writing process. Your authorial voice is very conversational, and I found it engaging to read, and yet many of us know that an incredible amount of hard work and re-writing goes into producing a book. Had you tried your hand at writing before you decided to write the book? And how easy was it to feel that you’d found your voice on the page, so to speak?

Financial Intimacy by Jacquette M. Timmons

Financial Intimacy cover image, courtesy of Chicago Review Press

I had a newsletter for several years before I had a blog, which preceded my book writing endeavor. So, I had about seven years behind me to practice finding my voice ‘on the page’ as you say. But, honestly, it took others to point out my voice to me. I didn’t set out saying this is my voice and let me make certain I’m writing in that voice. For me, it was very organic.

That said, I’m so grateful my voice is conversational. Yes, I have a very particular perspective about money. However, I never want to come across as the know-it-all expert who doesn’t value what someone else has to say or contribute. Nor do I want to be the person that doesn’t appreciate a perspective that may differ (or challenge) mine.

Plus, I think my day-to-day work adds to my conversational voice. Thanks to the one-to-one coaching I do with individuals and couples and the workshops I present, I’m given ample opportunities to practice talking about the emotions and math of money in a grounded and accessible manner.

What was one of the more challenging aspects of writing the book? And one of the joys? 

For me, the biggest challenge to writing my book was time. I got an advance, but not a large enough one that I could spend my time researching and writing, exclusively. In fact, I took on more work; in addition to continuing to run my business, I got a supplemental 9-5 job with a lot of flexibility.

For ten months, I had a fairly non-existent social life. When I wasn’t traveling to do a workshop or give a keynote, I split my days between my business and ‘daylighting’ job and from 6pm-11pm each weeknight I was either doing research, conducting an interview or writing. I treated Saturdays and Sundays as full work days and wrote those entire days. Friday evenings were the only nights I gave myself permission to ‘play’. And as the submission deadline neared, playtime became null and Fridays, Saturdays and Sundays became full writing days. (The one thing I didn’t give up, though, was my running schedule.)

While I wouldn’t want to write my next book with the same time challenge, I truly had fun writing Financial Intimacy. The joys were many, but if I must choose one it would be the privilege of going inside the lives of the women I profiled regarding a topic that is deeply personal and private.

And, finally, The Woolf special question: What is one of your favourite works of fiction, and why? 

Octavia E. Butler is one of my favorite authors, and I absolutely loved her fantasy novel, Kindred. For those unfamiliar, it is about a young, modern-day black woman who involuntarily, and without warning, gets ‘transported’ back in time to antebellum slavery—where she is a slave. Her ‘travels’ last only minutes or hours in current-day time, but they span months in the past.

The way Ms. Butler juxtaposes Dana’s (the main character’s) 20th-century life with her 19th-century life as a slave girl to address questions of identify, power, how we define (and redefine) history, family, ancestry, relationships, the notion of home, the definition of time, race, culture, love, hate, empathy and forgiveness is uncomfortable, artful and thought-provoking. Her writing is so completely riveting, as she beautifully and unflinchingly tells a story of the human condition.


Read: Financial Intimacy available on Amazon.

Listen: Jacquette talks, on the Productive Flourishing Podcast.

Author: Libby O'Loghlin

Novelist, social entrepreneur, nutrition and narrative coach. Creative Director of The Woolf Quarterly; Co-Founder of WriteCon and The Powerhouse Zurich. Nature is my jam.

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